Triethylamine → 2-((2S)-2-(4-(N-cyclohexyl-N-methylamino)-phenyl)morpholin-4-yl)-3-methyl-6-(4-pyridyl)-pyrimidin-4-one

HRID 424423Notes

Reaction equation

HRID 424423 reaction equation
[CH:1]1([N:7]([C:9]2[CH:14]=[CH:13][C:12]([C@@H:15]3[O:20][CH2:19][CH2:18][NH:17][CH2:16]3)=[CH:11][CH:10]=2)[CH3:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.Cl[C:29]1[N:34]([CH3:35])[C:33](=[O:36])[CH:32]=[C:31]([C:37]2[CH:42]=[CH:41][N:40]=[CH:39][CH:38]=2)[N:30]=1.ClC1C=CNC(=O)N=1>O1CCCC1>[CH:1]1([N:7]([C:9]2[CH:14]=[CH:13][C:12]([C@@H:15]3[O:20][CH2:19][CH2:18][N:17]([C:29]4[N:34]([CH3:35])[C:33](=[O:36])[CH:32]=[C:31]([C:37]5[CH:38]=[CH:39][N:40]=[CH:41][CH:42]=5)[N:30]=4)[CH2:16]3)=[CH:11][CH:10]=2)[CH3:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 112760814(3H)-Pyrimidinone, 2-chloro-3-methyl-6-(4-pyridinyl)-HCID 66704002(2S)-2-(4-(N-cyclohexyl-N-methylamino)phenyl)morpholineHCID 1785178106-Chloropyrimidin-2(1H)-one

Product 1

HCID 667039302-((2S)-2-(4-(N-cyclohexyl-N-methylamino)-phenyl)morpholin-4-yl)-3-methyl-6-(4-pyridyl)-pyrimidin-4-oneYield 75.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2S)-2-(4-(N-cyclohexyl-N-methylamino)phenyl)morpholine (4.47 g, 16.30 mmol) and triethylamine (3.1 ml, 22.2 mmol) in tetrahydrofuran (50 ml) was added 2-chloro-3-methyl-6-(4-pyridyl)-3H-pyrimidin-4-one (3.28 g, 14.82 mmol) portionwise. Upon disappearance of the chloropyrimidone, the reaction mixture was condensed under reduced pressure. The residue was partitioned between 1 N sodium hydroxide and dichloromethane. The organic layer was washed with water, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to give a pale yellow solid, which was recrystallized from ethanol to afford 2-((2S)-2-(4-(N-cyclohexyl-N-methylamino)-phenyl)morpholin-4-yl)-3-methyl-6-(4-pyridyl)-pyrimidin-4-one (5.15 g, 75.7%) as white crystals.

Workup

  1. customcondensed under reduced pressure
  2. customThe residue was partitioned between 1 N sodium hydroxide and dichloromethane
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give a pale yellow solid, which
  8. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-f01b814dcb8d493b8f34e254f468849f
Source dataset
uspto-grants-2012_01
Patent number
US08106045B2

Reaction notes

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